The present invention provides an alkoxide compound represented by the following general formula (1), a thin-film forming raw material containing the compound, and a method of producing a thin-film:

##STR00001##

where R.sup.1 and R.sup.2 each independently represent a hydrogen atom, an alkyl group having 1 to 5 carbon atoms, or a fluorine atom-containing alkyl group having 1 to 5 carbon atoms, R.sup.3 and R.sup.4 each independently represent an alkyl group having 1 to 5 carbon atoms, or a fluorine atom-containing alkyl group having 1 to 5 carbon atoms, R.sup.5 represents a hydrogen atom, a fluorine atom-containing group, or an alkyl group having 1 to 5 carbon atoms, R.sup.6 represents a fluorine atom-containing group, M represents a metal atom or a semimetal atom, and “n” represents the valence of the atom represented by M, provided that when M represents a copper atom, R.sup.3 and R.sup.4 each independently represent an alkyl group having 1 or 2 carbon atoms, and R.sup.5 represents a hydrogen atom.

The present disclosure is directed to organotin cluster compounds having formula (I) and their use as photoresists in extreme ultraviolet lithography processes. ##STR00001##

Provided is a thin-film forming raw material, which is used in an atomic layer deposition method, including an alkoxide compound represented by the following general formula (1):

##STR00001##

where R.sup.1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R.sup.2 and R.sup.3 each independently represent an alkyl group having 1 to 5 carbon atoms, and z.sup.1 represents an integer of from 1 to 3.

A semiconductor photoresist composition includes an organometallic compound represented by Chemical Formula 1, an organic acid having a vapor pressure of less than or equal to about 1.0 mmHg at 25° C., and a pKa of about 3 to about 5, and a solvent. A method of forming photoresist patterns utilizes the composition.

##STR00001##

Organotin clusters are described with the formula R.sub.3Sn.sub.3(O.sub.2CR′).sub.5−x(OH).sub.2+x(μ.sub.3-O) with 0≤x<2; R=branched or cycloalkyl with 1 to 31 carbon atoms; R′═H or alkyl with 1 to 20 carbon atoms. Three carboxylato ligands are bridging, and two OH ligands are bridging. The remaining two carboxylato ligands are in non-bridging configurations, and the non-bridging carboxylato ligands are exchangeable in solution. Solutions of these clusters are suitable for forming radiation sensitive coatings that can be used to pattern nanometer scale structures. The radiation sensitive coatings are particularly suitable for EUV patterning.

A semiconductor resist composition includes an organometallic compound represented by Chemical Formula 1 and a solvent: ##STR00001##
wherein, in Chemical Formula 1, R.sup.1 is an aliphatic hydrocarbon group, an aromatic hydrocarbon group, or an -alkyl-O-alkyl group, and R.sup.2 to R.sup.4 are each independently selected from —OR.sup.a and —OC(═O)R.sup.b. The semiconductor resist composition may have excellent solubility and storage stability.

The present disclosure is related to organometallic sandwich and half-sandwich tin (bearing η.sup.5-C.sub.5—Sn π bond) compounds as extreme ultraviolet (EUV) photoresist. Organometallic half-sandwich (η.sup.5-cyclopentadienyl)tin hydroxide oxide represented by the chemical formula (η.sup.5-C.sub.5R.sub.5)SnO(OH) and (η.sup.5-cyclopentadienyl)tin tri(hydroxide) represented by the chemical formula (η.sup.5-C.sub.5R.sub.5)Sn(OH).sub.3 are described including the methods for preparation and purification, wherein R is H, alkyl, alkenyl, alkynyl, cycloalkyl group with 1 to 20 carbon atoms, and aryl group with 6-20 carbon atoms. η.sup.5-cyclopentadienyl comprises η.sup.5-C.sub.5H.sub.5, and/or substituted η.sup.5-cyclopentadienyl η.sup.5-C.sub.5H.sub.4R, η.sup.5-C.sub.5H.sub.3R.sub.2, η.sup.5-C.sub.5H.sub.2R.sub.3, η.sup.5-C.sub.5HR.sub.4, and η.sup.5-C.sub.5R.sub.5. The solution compositions of organometallic sandwich and half-sandwich tin (bearing η.sup.5-C.sub.5—Sn π bond) compounds are suitable for EUV photoresists, and/or as the precursors of EUV photoresists for radiation sensitive coating and forming nanoscale patterns through photolithography.

The present disclosure is related to organometallic sandwich and half-sandwich tin (bearing η.sup.5-C.sub.5—Sn π bond) compounds as extreme ultraviolet (EUV) photoresist. Organometallic sandwich bis(cyclopentadienyl)tin oxide represented by the chemical formula (η.sup.5-C.sub.5R.sub.5).sub.2SnO, di(cyclopentadienyl)tin dialkoxide represented by the chemical formula (η.sup.5-C.sub.5R.sub.5).sub.2Sn(OR.sup.1)(OR.sup.2), and half-sandwich (cyclopentadienyl)tin triamide represented by the chemical formula (η.sup.5-C.sub.5R.sub.5)Sn(NR.sup.1.sub.2)(NR.sup.2.sub.2)(NR.sup.3.sub.2) are described including the methods for preparation and purification, wherein R.sup.1, R.sup.2, R.sup.3 are independently H, alkyl (linear or branched), alkenyl, alkynyl and cycloalkyl group with 1 to 20 carbon atoms, and aryl group with 6-20 carbon atoms. Sandwich and half-sandwich comprise cyclopentadienyl (C.sub.5H.sub.5), or substituted cyclopentadienyl (η.sup.5-C.sub.5H.sub.4R, η.sup.5-C.sub.5H.sub.3R.sub.2, η.sup.5-C.sub.5H.sub.2R.sub.3, η.sup.5-C.sub.5HR.sub.4, and η.sup.5-C.sub.5R.sub.5), R is H, alkyl, alkenyl, alkynyl, cycloalkyl group with 1 to 20 carbon atoms and aryl group with 6-20 carbon atoms. The solution compositions of organometallic sandwich and half-sandwich tin (bearing η.sup.5-C.sub.5—Sn π bond) compounds are suitable for EUV photoresists, and/or the precursors of EUV photoresists for radiation sensitive coating and forming nanoscale patterns through photolithography.

The present disclosure is related to organometallic sandwich and half-sandwich tin (bearing η.sup.5-C.sub.5—Sn π bond) compounds as extreme ultraviolet (EUV) photoresist. Organometallic sandwich di(cyclopentadienyl)tin dialkoxide represented by the chemical formula (η.sup.5-C.sub.5R.sub.5).sub.2Sn(OR.sup.1)(OR.sup.2), or half-sandwich (cyclopentadienyl)tin triamide represented by the chemical formula (η.sup.5-C.sub.5R.sub.5)Sn(NR.sup.1.sub.2)(NR.sup.2.sub.2)(NR.sup.3.sub.2) are described including the methods for preparation and purification, wherein R.sup.1, R.sup.2, R.sup.3 are independently H, linear or branched alkyl, alkenyl, alkynyl, or cycloalkyl group with 1 to 20 carbon atoms, or aryl group with 6-20 carbon atoms. Sandwich and half-sandwich groups comprise cyclopentadienyl (C.sub.5H.sub.5), or substituted cyclopentadienyl (η.sup.5-C.sub.5H.sub.4R, η.sup.5-C.sub.5H.sub.3R.sub.2, η.sup.5-C.sub.5H.sub.2R.sub.3, η.sup.5-C.sub.5HR.sub.4, or η.sup.5-C.sub.5R.sub.5). The solution compositions of organometallic sandwich and half-sandwich tin (bearing η.sup.5-C.sub.5—Sn π bond) compounds are suitable for EUV photoresists, and/or the precursors of EUV photoresists for radiation sensitive coating and forming nanoscale patterns through photolithography.

A semiconductor photoresist composition including an organometallic compound represented by Chemical Formula 1 and a solvent and a method of forming patterns using the same are disclosed.